data reports
ISSN 1600-5368
Crystal structure of (E)-1(anthracen-9-ylmethylidene)[2-(morpholin-4-yl)ethyl]amine
2. Experimental
2.1. Crystal data
Zeliha Atioğlu,a Mehmet Akkurt,b* Aliasghar Jarrahpour,c
Mehdi Mohammadi Chermahinic and Orhan
Büyükgüngörd
a
¤lke Education and Health Foundation, Cappadocia Vocational College, The
Medical Imaging Techniques Program, 50420 Mustafapaşa, Ürgüp, Nevşehir,
Turkey, bDepartment of Physics, Faculty of Sciences, Erciyes University, 38039
Kayseri, Turkey, cDepartment of Chemistry, College of Sciences, Shiraz University,
71454 Shiraz, Iran, and dDepartment of Physics, Faculty of Arts and Sciences,
Ondokuz Mayıs University, 55139 Samsun, Turkey. *Correspondence e-mail:
[email protected]
Received 18 August 2014; accepted 19 August 2014
V = 1790.10 (16) Å3
Z=4
Mo K radiation
= 0.07 mm1
T = 296 K
0.43 0.23 0.12 mm
C21H22N2O
Mr = 318.41
Monoclinic, P21
a = 6.0451 (3) Å
b = 17.8151 (10) Å
c = 16.8627 (8) Å
= 99.690 (4)
2.2. Data collection
Stoe IPDS 2 diffractometer
Absorption correction: integration
(X-RED32; Stoe & Cie, 2002)
Tmin = 0.980, Tmax = 0.993
22689 measured reflections
7325 independent reflections
2245 reflections with I > 2(I)
Rint = 0.116
Edited by D.-J. Xu, Zhejiang University (Yuquan Campus), China
2.3. Refinement
The title compound, C21H22N2O, crystallizes with two
independent molecules in the asymmetric unit. In both
molecules, the anthracene ring systems are almost planar,
with maximum deviations of 0.071 (8) and 0.028 (7) Å, and
make dihedral angles of 73.4 (2) and 73.3 (2) with the leastsquares planes formed by the four C atoms of the morpholine
rings, which adopt a chair conformation. An intramolecular
C—H interaction occurs. In the crystal, the packing is
stabilized by weak C—H O hydrogen bonds, which connect
pairs of molecules into parallel to the c axis, and C—H interactions.
R[F 2 > 2(F 2)] = 0.046
wR(F 2) = 0.076
S = 0.71
7325 reflections
433 parameters
Table 1
Hydrogen-bond geometry (Å, ).
Cg2 and Cg11 are the centroids of the C8/C9/C14–C16/C21 and C37–C42 rings,
respectively.
D—H A
i
Keywords: crystal structure; C—H interactions; Schiff bases; anthracene; morpholine; methanimine.
1 restraint
H-atom parameters constrained
max = 0.12 e Å3
min = 0.10 e Å3
C33—H33 O1
C13—H13 Cg11ii
C38—H38 Cg2
D—H
H A
D A
D—H A
0.93
0.93
0.93
2.59
2.73
2.79
3.344 (12)
3.567 (7)
3.548 (6)
138
150
139
Symmetry codes: (i) x þ 1; y 12; z þ 2; (ii) x þ 1; y; z.
CCDC reference: 1020122
1. Related literature
For background to the importance of Schiff bases and their
uses, see: Dhar & Taploo (1982); Witkop & Ramachandran
(1964); Solomon & Lowery (1993); Gerdemann et al. (2002).
Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: XAREA; data reduction: X-RED32 (Stoe & Cie, 2002); program(s)
used to solve structure: SHELXS2013 (Sheldrick, 2008); program(s)
used to refine structure: SHELXL2013 (Sheldrick, 2008); molecular
graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to
prepare material for publication: WinGX (Farrugia, 2012) and
PLATON (Spek, 2009).
Acknowledgements
The authors acknowledge the Faculty of Arts and Sciences,
Ondokuz Mayıs University, Turkey, for the use of the Stoe
IPDS 2 diffractometer (purchased under grant F.279 of the
University Research Fund). AJ and MMC thank the Shiraz
Acta Cryst. (2014). E70, o1045–o1046
doi:10.1107/S1600536814018807
Atioğlu et al.
o1045
data reports
University Research Council for financial support (grant No.
93-GR—SC-23).
Supporting information for this paper is available from the IUCr
electronic archives (Reference: XU5815).
o1046
Atioğlu et al.
C21H22N2O
References
Dhar, D. N. & Taploo, C. L. (1982). J. Sci. Ind. Res. 41, 501–506.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854.
Gerdemann, C., Eicken, C. & Krebs, B. (2002). Acc. Chem. Res. 35, 183–191.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.
Solomon, E. I. & Lowery, M. D. (1993). Science, 259, 1575–1581.
Spek, A. L. (2009). Acta Cryst. D65, 148–155.
Stoe & Cie (2002). X-AREA and X-RED32. Stoe & Cie, Darmstadt, Germany.
Witkop, B. & Ramachandran, L. K. (1964). Metabolism, 13, 1016–1025.
Acta Cryst. (2014). E70, o1045–o1046
supporting information
supporting information
Acta Cryst. (2014). E70, o1045–o1046
[doi:10.1107/S1600536814018807]
Crystal structure of (E)-1(anthracen-9-ylmethylidene)[2-(morpholin-4-yl)ethyl]amine
Zeliha Atioğlu, Mehmet Akkurt, Aliasghar Jarrahpour, Mehdi Mohammadi Chermahini and
Orhan Büyükgüngör
S1. Comment
Schiff bases are usually formed by the condensation of a primary amine with an active carbonyl. They are used as
pigments and dyes, catalysts, intermediates in organic synthesis, and as polymer stabilisers (Dhar & Taploo, 1982). Schiff
bases form an important class of organic compounds with a wide variety of biological properties (Witkop &
Ramachandran, 1964). Many studies have been reported regarding the biological activities of Schiff bases, including their
anticancer (Solomon & Lowery, 1993), antibacterial (Gerdemann et al., 2002), antifungal, and herbicidal activities.
Therefore, Schiff base (I) was synthesized and its X-ray structure is reported here.
As shown in Fig. 1, the asymmetric unit of the title compound (I) consists of two independent molecules (A, B). The
anthracene ring systems (C8–C21 and C29–C42) of the both molecules (A, B) are almostly planar [maximum deviations
= 0.069 (9) Å for C19 and 0.071 (8) Å for C12 in molecule A, and 0.028 (7) Å for C39 and C30 in molecule B]. They
make dihedral angles of 73.4 (2) and 73.3 (2)°, respectively, with the least-squares planes formed by the four C atoms of
the morpholine rings (C1–C4/N1/O1 and C22–C25/N3/O2), which adopts a chair conformation. The puckering
parameters of the morpholine rings are QT = 0.575 (9) Å, θ = 1.4 (9) °, φ = 142 (64) ° for molecule A, and QT = 0.569 (8)
Å, θ = 0.0 (8) °, φ = 223 (34) ° for molecule B, respectively.
The (C5–C6–N2–C7 and C26–C27–N4–C28) torsion angles of the bridge –C–C–N–C– groups is -103.0 (7) ° for
molecule A and 101.1 (6)° for molecule B. The bond lengths and angles in both molecules (A, B) may be regarded as
normal, and they are similar with each other.
In the crystal structure, weak C—H···O hydrogen bonds (Table 1, Fig. 2) which connect pairs of molecules into parallel
to the c axis, further stabilize the packing supported by C–H···π interactions (Table 1).
S2. Experimental
Reaction of anthracene-9-carbaldehyde (1.00 mmol) with 2-morpholinoethanamine (1.00 mmol) in refluxing ethanol gave
the title compound (I). Recrystallization from ethanol gave yellow crystals in 85% yield. Mp: 381–383 K. IR (KBr)
cm-1:1643 (C=N). 1H-NMR (250 MHz, CDCl3), δ (p.p.m.): 2.58 (CH2—N morpholine, t, 4H, J=5 Hz), 2.84 (morpholineCH2—CH2, t, 2H, J=7.5 Hz), 3.73 (CH2—O morpholine, t, 4H, J=5 Hz), 4.00 (morpholine-CH2—CH2, t, 2H, J=5 Hz),
7.37–7.94 (aromatic H, m, 9H), 8.45 (HC=N, s, 1H). 13CNMR (62.9 MHz, CDCl3), δ (p.p.m): 53.9 (CH2—N
morpholine), 58.9 and 59.6 (N—CH2—CH2—N), 67.0 (CH2—O morpholin), 124.9–131.2 (aromatic carbons), 161.4
(C=N).
Acta Cryst. (2014). E70, o1045–o1046
sup-1
supporting information
S3. Refinement
H atoms were located geometrically with C—H = 0.93 and 0.97 Å, and refined using a riding model with Uiso(H) =
1.2Ueq(C) for the aromatic and methylene H atoms. The crystal quality and data was not good enough so a sufficient
fraction of the unique data is above the 2 sigma level. A total of 749 estimated Friedel pairs were merged before
refinement and not used as independent data. The Flack parameter was found to be meaningless and was omitted.
Figure 1
View of the two molecules (A, B) of the title compound in the asymmetric unit with the atom-labelling scheme and 30%
probability displacement ellipsoids.
Acta Cryst. (2014). E70, o1045–o1046
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supporting information
Figure 2
Packing diagram of the title compound viewed down the a axis. Hydrogen bonds are indicated by broken lines. H atoms
not participating in hydrogen bonding have been omitted for clarity.
(E)-(Anthracen-9-ylmethylidene)[2-(morpholin-4-yl)ethyl]amine
Crystal data
C21H22N2O
Mr = 318.41
Monoclinic, P21
Hall symbol: P 2yb
a = 6.0451 (3) Å
b = 17.8151 (10) Å
c = 16.8627 (8) Å
β = 99.690 (4)°
V = 1790.10 (16) Å3
Z=4
F(000) = 680
Dx = 1.181 Mg m−3
Mo Kα radiation, λ = 0.71073 Å
Cell parameters from 10759 reflections
θ = 1.7–27.1°
µ = 0.07 mm−1
T = 296 K
Needle, yellow
0.43 × 0.23 × 0.12 mm
Data collection
Stoe IPDS 2
diffractometer
Radiation source: sealed X-ray tube, 12 x 0.4
mm long-fine focus
Plane graphite monochromator
Detector resolution: 6.67 pixels mm-1
ω scans
Absorption correction: integration
(X-RED32; Stoe & Cie, 2002)
Acta Cryst. (2014). E70, o1045–o1046
Tmin = 0.980, Tmax = 0.993
22689 measured reflections
7325 independent reflections
2245 reflections with I > 2σ(I)
Rint = 0.116
θmax = 26.5°, θmin = 1.7°
h = −7→7
k = −22→22
l = −21→21
sup-3
supporting information
Refinement
Refinement on F2
Least-squares matrix: full
R[F2 > 2σ(F2)] = 0.046
wR(F2) = 0.076
S = 0.71
7325 reflections
433 parameters
1 restraint
Hydrogen site location: inferred from
neighbouring sites
H-atom parameters constrained
w = 1/[σ2(Fo2) + (0.0001P)2]
where P = (Fo2 + 2Fc2)/3
(Δ/σ)max = 0.001
Δρmax = 0.12 e Å−3
Δρmin = −0.10 e Å−3
Special details
Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are
estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the
estimation of distances, angles and torsion angles
Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors.
Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to
zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs etc. and is not
relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those
based on F, and R-factors based on ALL data will be even larger.
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)
O1
N1
N2
C1
C2
C3
C4
C5
C6
C7
C8
C9
C10
C11
C12
C13
C14
C15
C16
C17
C18
C19
C20
C21
O2
N3
N4
x
y
z
Uiso*/Ueq
0.5030 (14)
0.6844 (9)
0.9321 (9)
0.4497 (12)
0.4292 (17)
0.7314 (19)
0.7548 (14)
0.7151 (11)
0.7207 (12)
0.9286 (11)
1.1260 (11)
1.2703 (12)
1.2220 (11)
1.3547 (14)
1.5368 (14)
1.5893 (12)
1.4558 (13)
1.4988 (12)
1.3580 (16)
1.4078 (14)
1.2768 (16)
1.0911 (18)
1.0344 (12)
1.1684 (13)
−0.0218 (13)
0.1892 (9)
0.4442 (8)
1.1304 (3)
1.0984 (3)
1.0010 (3)
1.0827 (4)
1.0681 (5)
1.1459 (5)
1.1610 (3)
1.1119 (3)
1.0390 (4)
0.9462 (4)
0.9000 (3)
0.8691 (3)
0.8797 (3)
0.8477 (4)
0.8018 (4)
0.7909 (3)
0.8241 (3)
0.8134 (4)
0.8435 (4)
0.8284 (4)
0.8546 (5)
0.8962 (5)
0.9135 (4)
0.8875 (4)
0.3492 (4)
0.3720 (2)
0.4611 (3)
0.8402 (4)
0.6979 (4)
0.5933 (3)
0.7044 (5)
0.7902 (6)
0.8339 (6)
0.7501 (6)
0.6140 (4)
0.5671 (4)
0.6392 (4)
0.6682 (5)
0.6193 (4)
0.5362 (5)
0.4871 (4)
0.5200 (5)
0.5997 (5)
0.6516 (5)
0.7345 (5)
0.7827 (4)
0.8665 (6)
0.9180 (5)
0.8894 (6)
0.8089 (5)
0.7520 (5)
0.9153 (4)
0.7801 (3)
0.6707 (3)
0.151 (3)
0.091 (3)
0.083 (2)
0.125 (4)
0.165 (5)
0.155 (6)
0.121 (4)
0.102 (3)
0.103 (3)
0.083 (3)
0.075 (3)
0.069 (3)
0.095 (3)
0.103 (3)
0.112 (4)
0.094 (3)
0.079 (3)
0.089 (3)
0.089 (4)
0.119 (4)
0.131 (5)
0.120 (4)
0.097 (4)
0.082 (3)
0.143 (3)
0.075 (2)
0.086 (2)
Acta Cryst. (2014). E70, o1045–o1046
sup-4
supporting information
C22
C23
C24
C25
C26
C27
C28
C29
C30
C31
C32
C33
C34
C35
C36
C37
C38
C39
C40
C41
C42
H1A
H1B
H2A
H2B
H3A
H3B
H4A
H4B
H5A
H5B
H6A
H6B
H7
H10
H11
H12
H13
H15
H17
H18
H19
H20
H22A
H22B
H23A
H23B
H24A
0.2622 (11)
0.2071 (17)
−0.0968 (13)
−0.0489 (11)
0.2383 (11)
0.2407 (11)
0.4249 (10)
0.6164 (11)
0.6443 (13)
0.4994 (12)
0.5272 (15)
0.7021 (18)
0.8488 (14)
0.8258 (13)
0.9658 (13)
0.9342 (13)
1.0851 (13)
1.0621 (14)
0.8943 (14)
0.7469 (11)
0.7638 (11)
0.39760
0.35650
0.27380
0.51790
0.82430
0.78320
0.66560
0.91050
0.85430
0.59320
0.59760
0.70340
0.79390
1.09900
1.32440
1.62200
1.71280
1.62360
1.53360
1.31310
1.00060
0.90770
0.42270
0.18780
0.25330
0.29020
−0.02060
Acta Cryst. (2014). E70, o1045–o1046
0.3138 (3)
0.3359 (5)
0.4068 (4)
0.3848 (3)
0.3506 (3)
0.4180 (3)
0.5193 (3)
0.5675 (3)
0.5896 (3)
0.5602 (4)
0.5804 (5)
0.6295 (4)
0.6564 (4)
0.6379 (3)
0.6628 (3)
0.6426 (4)
0.6725 (3)
0.6555 (4)
0.6070 (4)
0.5766 (3)
0.5937 (3)
1.03920
1.12520
1.05740
1.02440
1.10330
1.18910
1.20470
1.17250
1.13900
1.14300
1.00690
1.04990
0.93400
0.90860
0.85630
0.77870
0.76170
0.78570
0.79990
0.84420
0.91330
0.94250
0.30640
0.26700
0.29600
0.38080
0.45340
0.8388 (5)
0.9198 (5)
0.8585 (5)
0.7777 (4)
0.6997 (5)
0.6453 (4)
0.7114 (4)
0.7442 (4)
0.8261 (4)
0.8772 (5)
0.9561 (5)
0.9876 (5)
0.9425 (5)
0.8593 (5)
0.8079 (5)
0.7280 (5)
0.6783 (5)
0.5994 (5)
0.5655 (5)
0.6099 (4)
0.6937 (4)
0.67190
0.68430
0.79360
0.80930
0.85390
0.86690
0.73100
0.74780
0.61410
0.58740
0.57590
0.51000
0.65570
0.51400
0.43200
0.48600
0.62070
0.75760
0.88650
0.97270
0.92510
0.79130
0.84310
0.82130
0.95820
0.93880
0.87550
0.104 (3)
0.147 (5)
0.122 (4)
0.094 (3)
0.096 (3)
0.091 (3)
0.078 (3)
0.071 (3)
0.075 (3)
0.105 (4)
0.122 (4)
0.123 (4)
0.110 (4)
0.079 (3)
0.087 (3)
0.079 (3)
0.098 (4)
0.096 (4)
0.099 (3)
0.076 (3)
0.070 (3)
0.1490*
0.1490*
0.1980*
0.1980*
0.1850*
0.1850*
0.1450*
0.1450*
0.1220*
0.1220*
0.1230*
0.1230*
0.0990*
0.1140*
0.1230*
0.1340*
0.1130*
0.1080*
0.1420*
0.1570*
0.1440*
0.1160*
0.1250*
0.1250*
0.1760*
0.1760*
0.1470*
sup-5
supporting information
H24B
H25A
H25B
H26A
H26B
H27A
H27B
H28
H31
H32
H33
H34
H36
H38
H39
H40
H41
−0.25680
−0.13120
−0.09950
0.12550
0.38300
0.23450
0.11050
0.28310
0.38550
0.43080
0.71720
0.96590
1.08510
1.20080
1.15880
0.88130
0.63450
0.41450
0.33940
0.42420
0.31530
0.32580
0.40150
0.44920
0.53250
0.52700
0.56190
0.64390
0.68720
0.69420
0.70420
0.67640
0.59470
0.54450
0.85570
0.75990
0.73920
0.67470
0.70620
0.59010
0.64770
0.72120
0.85650
0.98900
1.04130
0.96600
0.82800
0.70110
0.56800
0.51130
0.58540
0.1470*
0.1130*
0.1130*
0.1150*
0.1150*
0.1090*
0.1090*
0.0930*
0.1270*
0.1460*
0.1480*
0.1330*
0.1040*
0.1170*
0.1150*
0.1190*
0.0910*
Atomic displacement parameters (Å2)
O1
N1
N2
C1
C2
C3
C4
C5
C6
C7
C8
C9
C10
C11
C12
C13
C14
C15
C16
C17
C18
C19
C20
C21
O2
N3
N4
U11
U22
U33
U12
U13
U23
0.189 (7)
0.086 (5)
0.075 (4)
0.085 (6)
0.210 (11)
0.194 (13)
0.113 (7)
0.093 (6)
0.101 (6)
0.083 (5)
0.060 (5)
0.082 (5)
0.095 (6)
0.120 (7)
0.127 (8)
0.092 (6)
0.081 (6)
0.090 (6)
0.122 (8)
0.100 (7)
0.110 (8)
0.145 (9)
0.084 (6)
0.070 (5)
0.181 (6)
0.068 (4)
0.076 (4)
0.123 (4)
0.067 (3)
0.098 (4)
0.114 (5)
0.141 (8)
0.161 (9)
0.075 (5)
0.102 (5)
0.124 (5)
0.096 (5)
0.075 (4)
0.073 (4)
0.097 (5)
0.109 (6)
0.105 (5)
0.092 (5)
0.062 (4)
0.090 (5)
0.093 (5)
0.146 (7)
0.175 (9)
0.152 (8)
0.111 (6)
0.082 (5)
0.148 (5)
0.072 (3)
0.094 (3)
0.161 (6)
0.122 (5)
0.077 (4)
0.184 (9)
0.178 (9)
0.115 (9)
0.171 (9)
0.110 (6)
0.079 (5)
0.070 (5)
0.086 (6)
0.056 (5)
0.098 (6)
0.076 (5)
0.112 (7)
0.105 (6)
0.095 (6)
0.082 (6)
0.054 (5)
0.111 (8)
0.097 (7)
0.068 (6)
0.097 (7)
0.088 (6)
0.107 (5)
0.083 (4)
0.086 (4)
0.003 (5)
−0.005 (3)
0.005 (3)
−0.032 (4)
−0.054 (7)
−0.002 (8)
−0.012 (4)
−0.004 (4)
0.002 (5)
−0.019 (4)
−0.024 (4)
−0.018 (4)
−0.001 (4)
−0.010 (5)
−0.001 (5)
0.008 (4)
−0.004 (4)
−0.007 (4)
−0.027 (5)
−0.003 (5)
0.017 (6)
−0.016 (6)
0.007 (4)
−0.005 (4)
−0.012 (5)
0.010 (3)
−0.010 (3)
0.085 (5)
0.022 (4)
0.012 (3)
0.049 (7)
0.127 (9)
0.044 (9)
0.017 (6)
0.018 (5)
0.001 (5)
0.014 (4)
−0.002 (5)
0.023 (4)
0.030 (5)
0.009 (5)
0.044 (6)
0.037 (6)
0.014 (5)
−0.002 (5)
0.021 (5)
0.021 (6)
−0.011 (6)
0.034 (6)
0.021 (5)
0.000 (5)
0.042 (5)
0.006 (3)
0.009 (3)
−0.019 (4)
−0.006 (3)
0.012 (3)
−0.019 (5)
−0.034 (7)
−0.033 (6)
−0.023 (5)
0.029 (5)
0.015 (4)
0.007 (4)
0.011 (4)
0.004 (4)
−0.003 (4)
0.008 (4)
0.004 (5)
−0.004 (5)
0.019 (4)
0.012 (5)
−0.005 (4)
−0.011 (6)
0.020 (6)
−0.020 (5)
−0.007 (5)
0.001 (4)
0.041 (4)
0.003 (3)
−0.013 (3)
Acta Cryst. (2014). E70, o1045–o1046
sup-6
supporting information
C22
C23
C24
C25
C26
C27
C28
C29
C30
C31
C32
C33
C34
C35
C36
C37
C38
C39
C40
C41
C42
0.088 (6)
0.159 (10)
0.134 (8)
0.085 (6)
0.084 (5)
0.091 (6)
0.079 (5)
0.075 (5)
0.089 (6)
0.116 (7)
0.136 (8)
0.184 (10)
0.145 (8)
0.093 (6)
0.087 (6)
0.088 (6)
0.105 (7)
0.096 (6)
0.108 (6)
0.082 (5)
0.066 (5)
0.079 (4)
0.148 (7)
0.104 (6)
0.086 (5)
0.071 (4)
0.105 (5)
0.078 (4)
0.050 (3)
0.067 (4)
0.115 (6)
0.152 (8)
0.117 (6)
0.106 (5)
0.062 (4)
0.089 (5)
0.068 (4)
0.074 (4)
0.078 (5)
0.100 (5)
0.086 (4)
0.048 (3)
0.137 (7)
0.113 (8)
0.138 (8)
0.112 (6)
0.133 (7)
0.078 (5)
0.078 (5)
0.086 (6)
0.070 (5)
0.088 (6)
0.082 (7)
0.072 (6)
0.077 (6)
0.082 (6)
0.084 (6)
0.088 (6)
0.112 (7)
0.120 (8)
0.101 (6)
0.059 (5)
0.094 (6)
−0.004 (4)
−0.007 (8)
0.000 (5)
0.005 (4)
−0.015 (4)
−0.011 (4)
−0.001 (4)
−0.001 (3)
0.012 (4)
−0.005 (5)
−0.023 (6)
0.002 (6)
−0.010 (5)
0.004 (4)
−0.010 (4)
−0.002 (4)
0.003 (4)
−0.013 (4)
0.002 (5)
0.010 (3)
−0.003 (3)
−0.007 (6)
−0.037 (8)
0.049 (6)
0.018 (5)
0.016 (5)
0.014 (4)
0.020 (4)
0.009 (5)
0.018 (5)
0.025 (6)
0.029 (6)
0.032 (6)
0.010 (5)
0.011 (5)
0.016 (5)
0.032 (5)
0.014 (6)
0.037 (6)
0.050 (6)
0.010 (4)
0.009 (5)
0.021 (5)
0.040 (6)
−0.010 (6)
0.001 (4)
−0.028 (4)
−0.011 (4)
−0.004 (4)
−0.003 (4)
−0.007 (4)
−0.004 (5)
−0.023 (5)
−0.009 (5)
−0.033 (4)
−0.011 (4)
−0.008 (4)
0.012 (4)
−0.015 (5)
0.001 (4)
0.012 (5)
−0.003 (3)
0.006 (4)
Geometric parameters (Å, º)
O1—C2
O1—C3
O2—C23
O2—C24
N1—C1
N1—C5
N1—C4
N2—C7
N2—C6
N3—C26
N3—C22
N3—C25
N4—C28
N4—C27
C1—C2
C3—C4
C5—C6
C7—C8
C8—C9
C8—C21
C9—C10
C9—C14
C10—C11
C11—C12
Acta Cryst. (2014). E70, o1045–o1046
1.420 (11)
1.429 (14)
1.393 (13)
1.425 (10)
1.468 (9)
1.477 (9)
1.440 (10)
1.248 (9)
1.448 (9)
1.486 (9)
1.450 (8)
1.451 (9)
1.260 (8)
1.452 (8)
1.496 (13)
1.469 (14)
1.524 (9)
1.464 (10)
1.409 (10)
1.411 (12)
1.395 (11)
1.411 (10)
1.370 (11)
1.408 (11)
C12—H12
C13—H13
C15—H15
C17—H17
C18—H18
C19—H19
C20—H20
C22—C23
C24—C25
C26—C27
C28—C29
C29—C30
C29—C42
C30—C31
C30—C35
C31—C32
C32—C33
C33—C34
C34—C35
C35—C36
C36—C37
C37—C38
C37—C42
C38—C39
0.9300
0.9300
0.9300
0.9300
0.9300
0.9300
0.9300
1.512 (12)
1.492 (11)
1.513 (9)
1.472 (9)
1.419 (9)
1.412 (9)
1.428 (11)
1.432 (10)
1.361 (12)
1.406 (13)
1.350 (13)
1.425 (12)
1.383 (11)
1.377 (12)
1.441 (11)
1.398 (10)
1.349 (12)
sup-7
supporting information
C12—C13
C13—C14
C14—C15
C15—C16
C16—C21
C16—C17
C17—C18
C18—C19
C19—C20
C20—C21
C1—H1A
C1—H1B
C2—H2A
C2—H2B
C3—H3A
C3—H3B
C4—H4A
C4—H4B
C5—H5B
C5—H5A
C6—H6A
C6—H6B
C7—H7
C10—H10
C11—H11
1.342 (12)
1.416 (11)
1.391 (12)
1.380 (11)
1.413 (12)
1.420 (12)
1.353 (13)
1.364 (14)
1.378 (13)
1.433 (11)
0.9700
0.9700
0.9700
0.9700
0.9700
0.9700
0.9700
0.9700
0.9700
0.9700
0.9700
0.9700
0.9300
0.9300
0.9300
C39—C40
C40—C41
C41—C42
C22—H22A
C22—H22B
C23—H23A
C23—H23B
C24—H24A
C24—H24B
C25—H25A
C25—H25B
C26—H26A
C26—H26B
C27—H27A
C27—H27B
C28—H28
C31—H31
C32—H32
C33—H33
C34—H34
C36—H36
C38—H38
C39—H39
C40—H40
C41—H41
1.381 (11)
1.368 (11)
1.432 (9)
0.9700
0.9700
0.9700
0.9700
0.9700
0.9700
0.9700
0.9700
0.9700
0.9700
0.9700
0.9700
0.9300
0.9300
0.9300
0.9300
0.9300
0.9300
0.9300
0.9300
0.9300
0.9300
C2—O1—C3
C23—O2—C24
C1—N1—C5
C4—N1—C5
C1—N1—C4
C6—N2—C7
C22—N3—C25
C22—N3—C26
C25—N3—C26
C27—N4—C28
N1—C1—C2
O1—C2—C1
O1—C3—C4
N1—C4—C3
N1—C5—C6
N2—C6—C5
N2—C7—C8
C9—C8—C21
C7—C8—C21
C7—C8—C9
C8—C9—C10
C10—C9—C14
108.5 (7)
111.1 (7)
112.4 (6)
112.8 (5)
107.0 (6)
116.7 (6)
108.5 (5)
110.8 (5)
111.4 (5)
116.4 (5)
110.1 (7)
111.7 (7)
111.0 (8)
112.3 (6)
112.1 (5)
109.6 (5)
123.3 (6)
119.9 (6)
115.1 (6)
125.0 (7)
119.3 (6)
118.9 (6)
C19—C18—H18
C20—C19—H19
C18—C19—H19
C21—C20—H20
C19—C20—H20
N3—C22—C23
O2—C23—C22
O2—C24—C25
N3—C25—C24
N3—C26—C27
N4—C27—C26
N4—C28—C29
C28—C29—C30
C28—C29—C42
C30—C29—C42
C29—C30—C31
C29—C30—C35
C31—C30—C35
C30—C31—C32
C31—C32—C33
C32—C33—C34
C33—C34—C35
120.00
119.00
119.00
120.00
120.00
110.0 (5)
111.3 (7)
109.6 (6)
111.1 (6)
111.9 (5)
109.6 (5)
123.1 (6)
119.0 (6)
120.2 (6)
120.8 (6)
120.1 (6)
120.3 (7)
119.5 (6)
120.4 (7)
119.7 (8)
122.1 (8)
120.5 (7)
Acta Cryst. (2014). E70, o1045–o1046
sup-8
supporting information
C8—C9—C14
C9—C10—C11
C10—C11—C12
C11—C12—C13
C12—C13—C14
C9—C14—C13
C13—C14—C15
C9—C14—C15
C14—C15—C16
C15—C16—C21
C17—C16—C21
C15—C16—C17
C16—C17—C18
C17—C18—C19
C18—C19—C20
C19—C20—C21
C8—C21—C20
C16—C21—C20
C8—C21—C16
C2—C1—H1A
C2—C1—H1B
N1—C1—H1A
N1—C1—H1B
H1A—C1—H1B
O1—C2—H2A
O1—C2—H2B
H2A—C2—H2B
C1—C2—H2B
C1—C2—H2A
O1—C3—H3B
O1—C3—H3A
C4—C3—H3B
H3A—C3—H3B
C4—C3—H3A
C3—C4—H4A
C3—C4—H4B
N1—C4—H4A
N1—C4—H4B
H4A—C4—H4B
H5A—C5—H5B
N1—C5—H5A
N1—C5—H5B
C6—C5—H5B
C6—C5—H5A
N2—C6—H6B
C5—C6—H6A
N2—C6—H6A
H6A—C6—H6B
Acta Cryst. (2014). E70, o1045–o1046
121.7 (7)
120.4 (6)
120.1 (7)
121.1 (7)
119.7 (7)
119.8 (7)
122.3 (7)
117.9 (7)
120.6 (7)
122.8 (7)
119.5 (8)
117.6 (8)
121.6 (8)
119.8 (8)
121.6 (9)
120.8 (8)
126.3 (7)
116.7 (7)
117.0 (7)
110.00
110.00
110.00
110.00
108.00
109.00
109.00
108.00
109.00
109.00
109.00
109.00
109.00
108.00
110.00
109.00
109.00
109.00
109.00
108.00
108.00
109.00
109.00
109.00
109.00
110.00
110.00
110.00
108.00
C30—C35—C34
C30—C35—C36
C34—C35—C36
C35—C36—C37
C36—C37—C38
C36—C37—C42
C38—C37—C42
C37—C38—C39
C38—C39—C40
C39—C40—C41
C40—C41—C42
C29—C42—C37
C29—C42—C41
C37—C42—C41
N3—C22—H22A
N3—C22—H22B
C23—C22—H22A
C23—C22—H22B
H22A—C22—H22B
O2—C23—H23A
O2—C23—H23B
C22—C23—H23A
C22—C23—H23B
H23A—C23—H23B
O2—C24—H24A
O2—C24—H24B
C25—C24—H24A
C25—C24—H24B
H24A—C24—H24B
N3—C25—H25A
N3—C25—H25B
C24—C25—H25A
C24—C25—H25B
H25A—C25—H25B
N3—C26—H26A
N3—C26—H26B
C27—C26—H26A
C27—C26—H26B
H26A—C26—H26B
N4—C27—H27A
N4—C27—H27B
C26—C27—H27A
C26—C27—H27B
H27A—C27—H27B
N4—C28—H28
C29—C28—H28
C30—C31—H31
C32—C31—H31
117.7 (7)
117.2 (7)
125.1 (7)
122.1 (7)
118.4 (7)
122.6 (7)
119.0 (7)
121.4 (7)
119.7 (8)
121.5 (7)
120.7 (6)
116.9 (6)
125.3 (6)
117.8 (6)
110.00
110.00
110.00
110.00
108.00
109.00
109.00
109.00
109.00
108.00
110.00
110.00
110.00
110.00
108.00
109.00
109.00
109.00
109.00
108.00
109.00
109.00
109.00
109.00
108.00
110.00
110.00
110.00
110.00
108.00
119.00
118.00
120.00
120.00
sup-9
supporting information
C5—C6—H6B
N2—C7—H7
C8—C7—H7
C11—C10—H10
C9—C10—H10
C10—C11—H11
C12—C11—H11
C11—C12—H12
C13—C12—H12
C14—C13—H13
C12—C13—H13
C16—C15—H15
C14—C15—H15
C16—C17—H17
C18—C17—H17
C17—C18—H18
110.00
118.00
118.00
120.00
120.00
120.00
120.00
119.00
119.00
120.00
120.00
120.00
120.00
119.00
119.00
120.00
C31—C32—H32
C33—C32—H32
C32—C33—H33
C34—C33—H33
C33—C34—H34
C35—C34—H34
C35—C36—H36
C37—C36—H36
C37—C38—H38
C39—C38—H38
C38—C39—H39
C40—C39—H39
C39—C40—H40
C41—C40—H40
C40—C41—H41
C42—C41—H41
120.00
120.00
119.00
119.00
120.00
120.00
119.00
119.00
119.00
119.00
120.00
120.00
119.00
119.00
120.00
120.00
C3—O1—C2—C1
C2—O1—C3—C4
C23—O2—C24—C25
C24—O2—C23—C22
C4—N1—C5—C6
C5—N1—C1—C2
C1—N1—C5—C6
C4—N1—C1—C2
C1—N1—C4—C3
C5—N1—C4—C3
C6—N2—C7—C8
C7—N2—C6—C5
C26—N3—C25—C24
C26—N3—C22—C23
C25—N3—C26—C27
C25—N3—C22—C23
C22—N3—C26—C27
C22—N3—C25—C24
C28—N4—C27—C26
C27—N4—C28—C29
N1—C1—C2—O1
O1—C3—C4—N1
N1—C5—C6—N2
N2—C7—C8—C9
N2—C7—C8—C21
C21—C8—C9—C10
C7—C8—C9—C14
C7—C8—C21—C20
C7—C8—C21—C16
C9—C8—C21—C20
C7—C8—C9—C10
−58.4 (9)
57.9 (9)
58.5 (8)
−58.3 (9)
159.8 (6)
179.0 (6)
−79.2 (7)
−56.7 (8)
58.0 (9)
−177.9 (7)
177.3 (6)
103.0 (7)
−179.6 (5)
−179.0 (6)
78.9 (6)
−56.4 (7)
−160.2 (5)
58.2 (6)
−101.1 (6)
177.7 (6)
59.5 (9)
−60.2 (9)
−73.5 (7)
−49.0 (10)
130.6 (7)
177.8 (6)
−179.0 (6)
2.1 (10)
−179.7 (6)
−178.3 (7)
−2.6 (9)
C15—C16—C21—C8
C15—C16—C17—C18
C17—C16—C21—C8
C21—C16—C17—C18
C15—C16—C21—C20
C16—C17—C18—C19
C17—C18—C19—C20
C18—C19—C20—C21
C19—C20—C21—C16
C19—C20—C21—C8
N3—C22—C23—O2
O2—C24—C25—N3
N3—C26—C27—N4
N4—C28—C29—C30
N4—C28—C29—C42
C28—C29—C30—C31
C28—C29—C30—C35
C42—C29—C30—C31
C42—C29—C30—C35
C28—C29—C42—C37
C28—C29—C42—C41
C30—C29—C42—C37
C30—C29—C42—C41
C29—C30—C31—C32
C35—C30—C31—C32
C29—C30—C35—C34
C29—C30—C35—C36
C31—C30—C35—C34
C31—C30—C35—C36
C30—C31—C32—C33
C31—C32—C33—C34
0.1 (11)
−178.9 (8)
−179.4 (7)
0.6 (12)
178.5 (7)
0.4 (13)
−1.1 (14)
0.7 (13)
0.4 (11)
178.6 (8)
57.7 (8)
−58.8 (7)
74.0 (7)
−131.7 (7)
51.0 (9)
5.2 (9)
−178.5 (6)
−177.5 (6)
−1.2 (9)
176.5 (6)
−0.9 (9)
−0.8 (9)
−178.2 (6)
179.1 (7)
2.8 (11)
−178.2 (6)
1.6 (9)
−2.0 (9)
177.8 (6)
−1.1 (12)
−1.6 (13)
Acta Cryst. (2014). E70, o1045–o1046
sup-10
supporting information
C21—C8—C9—C14
C9—C8—C21—C16
C10—C9—C14—C15
C14—C9—C10—C11
C8—C9—C14—C13
C10—C9—C14—C13
C8—C9—C10—C11
C8—C9—C14—C15
C9—C10—C11—C12
C10—C11—C12—C13
C11—C12—C13—C14
C12—C13—C14—C15
C12—C13—C14—C9
C13—C14—C15—C16
C9—C14—C15—C16
C14—C15—C16—C17
C14—C15—C16—C21
C17—C16—C21—C20
1.4 (9)
−0.1 (10)
−179.1 (6)
−0.9 (9)
176.6 (6)
0.2 (9)
−177.4 (6)
−2.7 (9)
2.1 (10)
−2.7 (11)
2.0 (11)
178.5 (7)
−0.8 (10)
−176.6 (7)
2.6 (10)
178.0 (7)
−1.4 (12)
−0.9 (11)
C32—C33—C34—C35
C33—C34—C35—C30
C33—C34—C35—C36
C30—C35—C36—C37
C34—C35—C36—C37
C35—C36—C37—C38
C35—C36—C37—C42
C36—C37—C38—C39
C42—C37—C38—C39
C36—C37—C42—C29
C36—C37—C42—C41
C38—C37—C42—C29
C38—C37—C42—C41
C37—C38—C39—C40
C38—C39—C40—C41
C39—C40—C41—C42
C40—C41—C42—C29
C40—C41—C42—C37
2.4 (13)
−0.6 (11)
179.6 (7)
0.1 (10)
179.9 (7)
178.6 (6)
−2.2 (11)
−179.4 (7)
1.4 (10)
2.5 (10)
−180.0 (6)
−178.3 (6)
−0.8 (9)
−1.6 (11)
1.3 (12)
−0.7 (11)
177.7 (6)
0.4 (9)
Hydrogen-bond geometry (Å, º)
Cg2 and Cg11 are the centroids of the C8/C9/C14–C16/C21 and C37–C42 rings, respectively.
D—H···A
D—H
H···A
D···A
D—H···A
C10—H10···N2
C33—H33···O1i
C41—H41···N4
C13—H13···Cg11ii
C38—H38···Cg2
0.93
0.93
0.93
0.93
0.93
2.44
2.59
2.48
2.73
2.79
3.039 (8)
3.344 (12)
3.044 (8)
3.567 (7)
3.548 (6)
122
138
119
150
139
Symmetry codes: (i) −x+1, y−1/2, −z+2; (ii) x+1, y, z.
Acta Cryst. (2014). E70, o1045–o1046
sup-11